Have you ever tried heated socks? (I’ve never used them…)
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For what it’s worth, I have respect for anyone who uses whatever gear is necessary to keep them comfortable on the bike, even if it looks dumb. If it gets you out on two wheels, more power to you, and screw naysayers.
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Sorry, I missed that…good luck!
My feet also get cold easily. I have summer shoes, fall/spring shoes that are a half size too big to allow for thick wool socks, and winter boots. Yes, that’s a lot of $$ but it’s worth it.
If there is any question about which shoe to wear, I go with the one that will keep my feet warmer.
My toes are fairly cold-sensitive and my fingers are ridiculously so — likely Reynaud’s, though I haven’t seen a doctor about it. Anyway, overdoing it on gloves and shoes takes care of it for me. For shoes, I use Lake 303 for temps below 40f, and cover those with neoprene booties below about 35f. Heavy and increased toe overlap, but worth it for comfort.
And for gloves, between 35f and 40f I use well-insulated bike or alpine ski gloves, and below 35f I use heated snowmobile gloves (FXR Recon). They have a huge gauntlet cuff and are very uncool and expensive, but I’m happy to continue riding all year long.
I have hundreds of dollars worth of standard booties and gloves that are inadequate, and I wish I had just bought the bullet earlier and went with “overkill” that works for me.
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I commute in the Midwest year round and had this issue last year big time. Then I got some old man winter boots and they are awesome. Yes I look a fred on a aero bike in the aerobars with boots on but hey my toes are warm…also heres is my breakdown
60s regular shoes
50s velotoze
40s over shoe
30s and below old man winters
Get a pair of proper winter boots. Like others have said, it doesn’t matter if it doesn’t look cool. The main thing is that you stay warm.
For temps you are riding in, consider these:
https://45nrth.com/products/ragnarok-reflective
I don’t have these, but I have the Wolvhammers, and a few friends have the Wolfgars. So I’d say 45Nrth makes pretty good stuff.
Also, it’s pretty widely known that much extremity heat is lost through the head. Wearing a hat or beanie under helmet may change the situation for you.